U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H19N2O5S.Na
Molecular Weight 386.3997
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUMETANIDE SODIUM

SMILES

CCCCNc1cc(cc(c1Oc2ccccc2)S(=O)(=O)N)C(=O)[O-].[Na+]

InChI

InChIKey=QDFGOJHAQZEYQL-UHFFFAOYSA-M
InChI=1S/C17H20N2O5S.Na/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13;/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H19N2O5S
Molecular Weight 363.4099
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including: http://www.rxlist.com/bumex-drug/side-effects-interactions.htm https://www.drugs.com/cdi/bumetanide.html http://www.wikidoc.org/index.php/Bumetanide_(oral)

Bumetanide is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. It blocks the reabsorption of sodium and fluid from the kidney's tubules. The most frequent clinical adverse reactions considered probably or possibly related to bumetanide are muscle cramps (seen in 1.1% of treated patients), dizziness (1.1%), hypotension (0.8%), headache (0.6%), nausea (0.6%) and encephalopathy (in patients with preexisting liver disease) (0.6%). One or more of these adverse reactions have been reported in approximately 4.1% of patients treated with Bumex (bumetanide). Lithium should generally not be given with diuretics (such as Bumex (bumetanide)) because they reduce its renal clearance and add a high risk of lithium toxicity. Bumex (bumetanide) may potentiate the effect of various antihypertensive drugs, necessitating a reduction in the dosage of these drugs.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.0 µM [IC50]
Target ID: Q9UP95|||O60632
Gene ID: 6560.0
Gene Symbol: SLC12A4
Target Organism: Homo sapiens (Human)
60.0 µM [IC50]
Target ID: Q9H2X9
Gene ID: 57468.0
Gene Symbol: SLC12A5
Target Organism: Homo sapiens (Human)
55.0 µM [IC50]
Target ID: Q13621
Gene ID: 6557.0
Gene Symbol: SLC12A1
Target Organism: Homo sapiens (Human)
4.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BUMEX

Approved Use

Bumetanide Injection is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. Almost equal diuretic response occurs after oral and parenteral administration of bumetanide. Therefore, if impaired gastrointestinal absorption is suspected or oral administration is not practical, bumetanide should be given by the intramuscular or intravenous route. Successful treatment with bumetanide following instances of allergic reactions to furosemide suggests a lack of cross-sensitivity.

Launch Date

4.1523839E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
42 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
111.38 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
167.34 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
258 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.88 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3%
BUMETANIDE serum
Homo sapiens
population: HEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Disc. AE: Hypokalemia, Anorexia...
AEs leading to
discontinuation/dose reduction:
Hypokalemia (moderate, 14.3%)
Anorexia (moderate)
Fatigue (moderate)
Polyuria (moderate, 4.8%)
Sources: Page: p.4
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources: Page: p.597
unhealthy, 22-72
n = 18
Health Status: unhealthy
Condition: Renal edema
Age Group: 22-72
Sex: M+F
Population Size: 18
Sources: Page: p.597
AEs

AEs

AESignificanceDosePopulation
Hypokalemia moderate, 14.3%
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Polyuria moderate, 4.8%
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Anorexia moderate
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Fatigue moderate
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer










Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
modest [IC50 348 uM]
yes [IC50 0.75 uM]
yes [IC50 7.6 uM]
yes [IC50 77.5 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
External Cl(-)-dependent formation of watery vacuoles by long-term hypotonic shock in 3T3-L1 cells.
2001
Solubilization and stability of bumetanide in vehicles for intranasal administration, a pilot study.
2001
Effect of chloride channel blockers on anti-IgE-stimulated histamine and IL-4/IL-13 release from human basophils.
2001 Apr
Differential roles of the sodium-calcium exchanger in renin secretion and renal vascular resistance.
2001 Aug
Effects of thiazide- and loop-diuretics, alone or in combination, on calcitropic hormones and biochemical bone markers: a randomized controlled study.
2001 Aug
Loop diuretics and in vitro relaxation of human fetal and newborn mouse airways.
2001 Aug
"Avian-type" renal medullary tubule organization causes immaturity of urine-concentrating ability in neonates.
2001 Aug
Protection of ischemic myocardium in diabetics by inhibition of electroneutral Na+-K+-2Cl- cotransporter.
2001 Aug
Insulin-independent, MAPK-dependent stimulation of NKCC activity in skeletal muscle.
2001 Aug
Cl(-)-dependent secretory mechanisms in isolated rat bile duct epithelial units.
2001 Aug
Functional and molecular characterization of the K-Cl cotransporter of Xenopus laevis oocytes.
2001 Aug
Alterations in airway ion transport in NKCC1-deficient mice.
2001 Aug
Contractile regulation of the Na(+)-K(+)-2Cl(-) cotransporter in vascular smooth muscle.
2001 Aug
Optical method for quantifying rates of mucus secretion from single submucosal glands.
2001 Aug
Contribution of the Na-K-Cl cotransporter on GABA(A) receptor-mediated presynaptic depolarization in excitatory nerve terminals.
2001 Aug 15
Cisplatin-induced apoptosis of mesothelioma cells is affected by potassium ion flux modulator amphotericin B and bumetanide.
2001 Aug 15
Potentiation of urinary atrial natriuretic peptide interferes with macula densa function.
2001 Aug 15
Growth factors stimulate the Na-K-2Cl cotransporter NKCC1 through a novel Cl(-)-dependent mechanism.
2001 Dec
Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter.
2001 Jul
Effects of the potassium channel blocker barium on sodium and potassium transport in the rat loop of Henle in vivo.
2001 Jul
Epinephrine-induced increases in [Ca2+](in) and KCl-coupled fluid absorption in bovine RPE.
2001 Jul
Forskolin activation of apical Cl- channel and Na+/K+/2Cl- cotransporter via a PTK-dependent pathway in renal epithelium.
2001 Jul 27
Na+-K+-Cl- cotransporter in rat focal cerebral ischemia.
2001 Jun
Two further British families with the 'cryohydrocytosis' form of hereditary stomatocytosis.
2001 Jun
Determination and characterization of diuretics in human urine by liquid chromatography coupled to pneumatically assisted electrospray ionization mass spectrometry.
2001 Jun
cAMP-dependent fluid secretion in rat inner medullary collecting ducts.
2001 Jun
Endogenous and exogenous Na-K-Cl cotransporter expression in a low K-resistant mutant MDCK cell line.
2001 Jun
Application of multiple response optimization technique to extended release formulations design.
2001 Jun 15
K(+) transport in red blood cells from human umbilical cord.
2001 Jun 6
Ca++ regulation of paracellular permeability in the middle intestine of the eel, Anguilla anguilla.
2001 Mar
Pharmacokinetics and pharmacodynamics of intravenous bumetanide in mutant Nagase analbuminemic rats: importance of globulin binding for the pharmacodynamic effects.
2001 May
HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway.
2001 May
Diverging effects of 5-HT3 receptor antagonists ondansetron and granisetron on estramustine-inhibited cellular potassium transport.
2001 May
Pulmonary oedema after ophthalmic regional anaesthesia in an unfasted patient undergoing elective surgery.
2001 May
Role of renocortical cyclooxygenase-2 for renal vascular resistance and macula densa control of renin secretion.
2001 May
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Ethanol-induced swelling in neonatal rat primary astrocyte cultures.
2001 May 11
Role of Cl- current in endothelin-1-induced contraction in rabbit basilar artery.
2001 Nov
Vacuolation induced by VacA toxin of Helicobacter pylori requires the intracellular accumulation of membrane permeant bases, Cl(-) and water.
2001 Nov 23
Ionic mechanisms of GABA-induced long-term potentiation in the rat superior colliculus.
2001 Oct
Mechanism(s) of chloride transport in human distal colonic apical membrane vesicles.
2001 Oct
Mechanism of substance P-induced liquid secretion across bronchial epithelium.
2001 Sep
Contribution of the Na(+)-K(+)-2Cl(-) cotransporter (NKCC1) to transepithelial transport of H(+), NH(4)(+), K(+), and Na(+) in rat outer medullary collecting duct.
2002 Apr
Renal Na-K-Cl cotransporter NKCC2 in Dahl salt-sensitive rats.
2002 Apr
NKCC2: a drug target in hypertension.
2002 Apr
Steroids modulate transepithelial resistance and Na(+) absorption across cultured porcine vas deferens epithelia.
2002 Apr
Chloride transport in rabbit esophageal epithelial cells.
2002 Apr
Interleukin-13 induces a hypersecretory ion transport phenotype in human bronchial epithelial cells.
2002 Feb
Intrinsic optical signals in the rat optic nerve: role for K(+) uptake via NKCC1 and swelling of astrocytes.
2002 Feb
Effects of butyrate on active sodium and chloride transport in rat and rabbit distal colon.
2002 Feb 15
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Parenteral Administration: The usual initial dose is 0.5 to 1 mg intravenously or intramuscularly. Intravenous administration should be given over a period of 1 to 2 minutes. If the response to an initial dose is deemed insufficient, a second or third dose may be given at intervals of 2 to 3 hours, but should not exceed a daily dosage of 10 mg.
The usual total daily dosage of Bumetanide is 0.5 mg to 2 mg and in most patients is given as a single dose.
Route of Administration: Other
10 uM of bumetanide reduced amplitude and frequency of ictal-like events (ILE) induced by 8.5 mM K(+), but it increased the frequency of ILE induced by 1 microM kainate.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:10:47 UTC 2021
Edited
by admin
on Sat Jun 26 05:10:47 UTC 2021
Record UNII
1QC8KM52D1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUMETANIDE SODIUM
Common Name English
BUMETANIDE SODIUM SALT
Common Name English
SODIUM 3-(AMINOSULFONYL)-5-(BUTYLAMINO)-4-PHENOXYBENZOATE
Systematic Name English
BENZOIC ACID, 3-(AMINOSULFONYL)-5-(BUTYLAMINO)-4-PHENOXY-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
28434-74-4
Created by admin on Sat Jun 26 05:10:47 UTC 2021 , Edited by admin on Sat Jun 26 05:10:47 UTC 2021
PRIMARY
CAS
28434-74-4
Created by admin on Sat Jun 26 05:10:47 UTC 2021 , Edited by admin on Sat Jun 26 05:10:47 UTC 2021
PRIMARY
ECHA (EC/EINECS)
249-015-6
Created by admin on Sat Jun 26 05:10:47 UTC 2021 , Edited by admin on Sat Jun 26 05:10:47 UTC 2021
PRIMARY
FDA UNII
1QC8KM52D1
Created by admin on Sat Jun 26 05:10:47 UTC 2021 , Edited by admin on Sat Jun 26 05:10:47 UTC 2021
PRIMARY
PUBCHEM
23696786
Created by admin on Sat Jun 26 05:10:47 UTC 2021 , Edited by admin on Sat Jun 26 05:10:47 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE